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The fix is two-part. First of all, I changed one behavior so IE Edge works like Webkit. In previous IEs, clicking the image in contenteditable selected it, now it does not, so we use same mechanism for selecting like in Chrome etc.

I found out that the problem with disappearing selection is, in fact, a native one (see attachment:13386.html​​). Older IEs display resize handlers once clicked an image. But Edge does nothing and I guess that this is the consequence of the move ​described on Edge blog:

Our investigation revealed that the problem Medium was encountering was due to a non-standard legacy feature involving object-selection, which shipped in Internet Explorer 5. [...] It gave the user the option to re-size any element which had layout on first click, and on second click would allow them to edit, if the element were editable.
[...] With this we decided to remove nearly 1500 lines of C++ code from the browser’s engine, as well as any dependencies.

I simplified the solution by @scofalik in ​branch:t/13386b. I discovered that an extra click listener is obsolete if selection.selectElement() is called in tiemout on mousedown in Edge.

There's no need for any timeout. You simply need to prevent a default action of that click to be able to make a selection. This is pretty logical. Of course, there's an inconsistency between engines, but I was struggling with reporting it, because comparing FF, Chrome, IE11 and Edge everything works differently on every single browser. On FF for instance, clicking selects an image, on Chrome it doesn't, but event does not have to be cancelled, on IE11 you have the control selection and on Edge you don't have it, but clicking does nothing.

As preventing default action sounds rather well, we can add it on Edge only, or we can think about adding it on all browsers, but I'm a little bit worried about some issues with focus. Preventing a default action may prevent focusing the editor if it wasn't focused before clicking. Therefore, this must be checked (manual test with inline editor is needed).

I changed .env.version to .env.edge and listening on click to mouseup. These changes were dictated by the fact that long mousedown did result in image losing selection (on both 13386 and 13386b but it is impossible to fix on 13386b).

Edit: I also rebased with master and did minor change in test's .md file.